Decavanadate‐Catalyzed Oxidative Cross‐Dehydrogenative Coupling: an Efficient and Sustainable Approach toward P(O)─S Bond Formation
Abstract
Abstract A convenient green protocol has been developed for the cross‐dehydrogenative coupling between thiols and P(O)−H compounds using decavanadate anion as the catalyst at room temperature under open‐flask conditions. The reaction proceeds efficiently in water or ethanol without any assistance of heat, light, electricity, or unfriendly additives and tolerates a broad spectrum of functional groups, delivering the desired products in up to 95% yield. Importantly, the decavanadate catalyst can be easily recycled in gram‐scale synthesis at least six times without a significant decline in reaction yield. Further, mechanistic investigations evidence the formation of tetravalent vanadium‐hydroxo‐species in the reaction process and reveal that the P(O)−S dehydrogenative coupling is enabled via a V V to V IV catalytic cycle.
Article Details
Authors (10)
Jian Lei
Department of Public Foundation
Zhenliang Yu
Jiangxi Provincial Key Laboratory of Tissue Engineering School of Pharmacy Gannan Medical University Ganzhou 341000 P.R. China
Shi Ru
Key Lab of Organic Optoelectronics & Molecular Engineering of Ministry of Education Department of Chemistry Tsinghua University Beijing 100084 P.R. China
Zixiu Wang
Jiangxi Provincial Key Laboratory of Tissue Engineering School of Pharmacy Gannan Medical University Ganzhou 341000 P.R. China
Shan Li
Institute of Solid State Chemistry, Department of Physical Chemistry, Beijing Advanced Innovation Center for Materials Genome Engineering
Nianhua Luo
Jiangxi Provincial Key Laboratory of Tissue Engineering School of Pharmacy Gannan Medical University Ganzhou 341000 P.R. China
Jiuzhong Huang
Jiangxi Provincial Key Laboratory of Tissue Engineering School of Pharmacy Gannan Medical University Ganzhou 341000 P.R. China
Xiaopeng Peng
Jiangxi Provincial Key Laboratory of Tissue Engineering School of Pharmacy Gannan Medical University Ganzhou 341000 P.R. China
Feng Jiang
State Key Laboratory of Integrated Optoelectronics, JLU Region, College of Electronic Science and Engineering, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. China
Yongge Wei
Department of Chemistry, Key Lab of Organic Optoelectronics and Molecular Engineering of Ministry of Education